


I Feel Pretty/Unpretty

by asphaltcowgrrl



Series: Wes in a Dress [1]
Category: Common Law
Genre: Crossdressing Kink, M/M
Language: English
Status: Completed
Published: 2013-10-11
Updated: 2013-10-11
Packaged: 2017-12-29 02:43:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,042
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/999907
Author URL: https://archiveofourown.org/users/asphaltcowgrrl/pseuds/asphaltcowgrrl
Summary: <blockquote class="userstuff">
              <p>Wes has a very special way of banishing his loneliness... with a touch of lipstick and a pretty dress.</p>
            </blockquote>





	I Feel Pretty/Unpretty

**Author's Note:**

> I'm still not sure if I should be proud of myself for this or insanely ashamed... Either way, I hope you enjoy and laugh as much as I did while writing it. The title comes from a mashup of "I Feel Pretty" and "Unpretty" performed on Glee. Look it up, it's pretty darn good.

_Unpretty_

“I guess it’s a night,” Travis said, slapping Wes on the back.

The blonde paused, an invitation on the tip of his tongue.  “Hey Travis?”

“Mmm?”  His partner was digging around in his desk looking for heaven only knew what.

“Got time for some food before heading home?”

Travis shook his head.  “Naw man, I’ve got a hot date.”  He sang those last two words in an annoyingly high falsetto, causing Wes to grimace. 

“Ah,” he hedged.  “Okay, have a good – whatever.”

He looked up, a huge grin plastered on his silly face.  “You know I will.”

Wes watched him leave, sad for once to see the aggravating man go somewhere without him.  Sighing, he spotted Kendall on her way out of the precinct for the night.  “Hey Kendall,” he called, hating himself for being so needy. 

“Yeah?  What’s up, detective?”  She titled her pretty red head, smile tugging at the corner of her mouth. 

“I was, well, I was headed out to grab some dinner, want to come along?”

She frowned prettily.  “I’m sorry, Wes, but I’ve got a date with this new RPG I downloaded last night.  Maybe next time?”

He nodded, trying to hide his disappointment.  “Sure, Kendall.  Go kill some orcs or something.”

Her hesitant smile turned into an all-out grin.  “I’ll even kill a few in your name.”  She blew him a kiss and left him standing alone. 

It had been a long time since he’d felt this lonely.  He figured the last time was during law school, before he’d met Alex and fallen in love with her.  Even since their divorce, he hadn’t felt as utterly isolated as he did tonight.  So why now? 

Wes shook the thoughts from his head, grabbed the suit jacket that was draped over the back of his chair, and headed out to his car.  Locked securely inside, he started the ignition and reached for the glove box.  He hesitated for a moment, drawing his hand back, but figured no one would ever possibly know so what the hell, right?  With a sigh, he tugged the CD-R out of its hiding place and slipped the unlabeled piece of media into his stereo. 

In one manner or another, he’d always had one of these – a CD, a cassette tape, a playlist purposely mislabeled on his iPod – an emergency mood-booster made of music.  The older he got, the more humiliating the music selections became.  His only worry, however, was that it did its job.  And so far, tonight it was doing just that. 

“Baby I got plans tonight you don’t know nothin’ about,” he sang along, a grin forming on his mouth as an idea began to take shape in his brain.  “So I’m going out tonight in my red high heels.”

 

_Pretty_

It had been a long, _long_ time since he’d even so much as contemplated doing what he was about to do.  But as he lived and breathed, he was thinking about doing it again.  _Tonight_.  He took in a deep breath, slowly letting it out in the yogic manner before reaching for the box he had buried at the back of his hotel closet.  How he’d kept it for so many years without Alex stumbling across it was still a mystery, but that was a conundrum for another time.  He had more important things to concentrate on right now. 

Humming, Wes took the box to the bathroom and set it on the pristine countertop.  Shimmying out of his work clothes, he sat on a stool hijacked out of the kitchen and stared into the mirror.  The leather seat was astoundingly cold against his naked backside.  It was going to be tough to pull off, he realized.  His jaw, while still smooth from that morning’s shave, had broadened and sharpened over the years since his last time.  But he thought he could make it work.  All he needed was a shower and a little help from some friends. 

Stepping into the shower, he let the steaming hot water wash over him, sluicing his cares down the drain and leaving a new person behind.  Closing his eyes, he ducked his head under the scalding stream, thinking about the first time.  He’d been seventeen and alone, much like he was tonight.  Wes had known he shouldn’t have let the older boy talk him into it, but he had.  And he’d discovered very quickly that he liked the freedom becoming another person allowed him. 

With a twist of his wrist, he shut off the water, grabbed one extra fluffy towel the hotel was famous for, and carefully dried from head to toe.  Donning an equally fluffy white robe, he stepped out of the shower and parked himself back on the stool.  Opening the case, he grinned. 

“I feel pretty, oh so pretty.  I feel pretty and witty and bright,” he sang, crooked grin lighting up his face.  He reached for a small bottle of foundation and put it back.  His skin had cleared since those early days and he didn’t think he’d need it tonight.  Instead, he chose a charcoal grey eyeliner.  “And I pity any girl who isn’t me tonight.”

 

_Unpretty_

Wes looked at the tube of lipstick in his hand and he frowned.  Self-doubt overwhelmed him suddenly, taking away his breath with its intensity.  He dumped the lipstick back into his case angrily.  Who was he kidding anyway?  He couldn’t get a woman – or a man, for that matter – to give him a second look in his high dollar suits and perfectly styled hair.  How stupid was he to think that he could turn anyone’s head in a dress, no matter how much makeup he spackled on?  He wasn’t some hard up teenaged law student any longer, just desperate for a few extra bucks so he could have a little meat for dinner once in a while.      

He chuckled at that last thought.  Wes had participated – and won – more than a few drag competitions back in the day because a boy had to pay for law school somehow, right?  It never seemed to matter to any of the men, and even fewer of the women, that he’d been prancing around on stage in feathers and heels all night.  He’d gotten more than the occasional bit of meat those nights. 

But he was thirty-six years old now and things were different.  When did he officially reach ‘too old’ for dress up?  That crooked smile crept back onto his face.  Whatever that answer was, it wasn’t going to be tonight. 

 

_Pretty_

A fleeting thought consisting of Travis’ reaction to this scenario flitted through his mind as he sat applying mascara to his nearly invisible blonde lashes.  Travis was the last thing that should be on his mind, he reminded himself.  But on the bright side, Travis prided himself on being pretty open when it came to sex and sexuality so he figured that, although he knew he’d never live it down, he doubted Travis would ever hold it against him.    

Wes leaned back in and attacked the lashes of his other eye with the mascara.  He wondered if Alex ever figured out he’d stolen this gorgeous copper sunset out of her ‘pretty girl bag’. It was doubtful when you considered the amount of makeup that woman owned – Sephora, Lancome, MAC – you name it, she had it.  What was one dual eyeliner and mascara tube in the grand scheme of things?

He gave his lashes a flutter and assessed himself in the mirror.  The dark touch of the eyeliner beneath his coppery lashes really made his eyes pop.  With just a touch of a complimentary copper eye shadow, he was set.  All he needed was something for his lips…

Settling for an understated pink close to his natural lip hue, he ran the stick along the curve of his bottom lip and then up and around his upper.  Puckering to make sure he’d done it right, he smiled.  Still hadn’t lost his touch.  Giving himself the once over, he called it good and stood.  Turning he spied his dress hanging from the towel rack behind him. 

It was a strappy summer dress, white cotton with a delicate pattern of pastel wildflowers.  Nothing fancy but just feminine enough to get the job done.  He lifted it off the hanger, and stepped into the slip of fabric.  

A knock sounded at his door.  Wes sighed, deciding to ignore it.  He had no desire to talk to anyone who actually knew who he was tonight.  When a second pound landed on the door, he shook his head and lifted the dress over his hips, slipping his arms through the spaghetti straps.  He zipped and turned, skirt twirling around his bare knees.  Nodding his approval of himself, he strutted out into the living room. 

_Unpretty_

The pounding at the door stopped finally.  Wes gave a mental eye roll and strolled through the living area into the kitchen.  He really wasn’t very hungry, but sometimes wandering through his hotel room did him some good.  Movement eased stress, he had been told.  Exiting the kitchen, he reentered the living room, stopping dead in his tracks.

Travis Marks stood in his entryway, spare room key in one hand. 

“Holy shit, Wes,” he breathed.  “Is that really you?”

Wes opened his mouth to deny it, but what could he say, really?  “Travis –,” he began, then faltered.

Travis swallowed hard, closing the door behind him.  “Do you have shoes,” he whispered.

“What?”  Wes was expecting an explosion, not a question of footwear.

“Shoes.  Heels.  Do you have a pair?”

Wes ran the tip of his tongue along his painted lower lip.  “Yeah.  But look, Travis this…”  

Travis raked his gaze across his partner’s body, from coiffed hair to his pretty pink toenails.  “Put them on.”

Wes was stunned.  Slipping on the low white heels he’d picked for this dress, he shot a look at his partner.  “If you’re doing this for more ammunition, let me tell you something.  This…”

“This is the hottest fucking thing I’ve ever seen you wear,” Travis finished for him.  “And let me tell you, you look pretty fucking tasty most days.”

The blonde’s mouth snapped shut.  How did you respond to that kind of thing anyway?  Wes went for the obvious.  “Why are you even here?  And that key was for emergencies only!”

Travis shrugged, unable to tear his eyes off Wes’ slim hips covered in pretty floral.  “Date cancelled at the last minute,” he admitted.  “And it was an emergency, you weren’t answering!  You _always_ answer, even if it’s to tell me to fuck off.”

“And now you know why I didn’t,” he whispered, ashamed all over again. 

 

_Pretty_

Travis stepped closer, lifting Wes’ chin with a finger.  “You look amazing.  And your makeup is perfect.  You’ve done this before, haven’t you?”  That Wes wouldn’t meet his gaze was his first clue.  He gave his partner some room before saying, “Turn around.”

“What?”  Wes’ head snapped up quickly.

“Gimme a twirl, beautiful,” he repeated, spinning one finger in the air for emphasis. 

Wes licked his bottom lip again but did as he was told.  He held his arms out to the side and turned slowly so that his skirt flowed out around him as he turned.  “Like that?”

“Mmph,” Travis grunted from right behind him, “God yes.” 

He slung one arm tightly around Wes’ waist, pulling him backward against his body.  The press of Travis’ firm cock against his ass startled a gasp out of him.  Heat flooded his face as blood flooded his own cock.  “Please,” he begged, not knowing if he wanted Travis to flee or come even closer.

“Please what,” Travis taunted, nipping at the exposed skin of Wes’ neck.  “God you smell so good, too.  Like coconut and lime.”

Wes let his head fall back against his partner’s.  Travis’ hand cupped his cock through the dress, rubbing slowly, teasing.  “You didn’t answer my question, ‘please what’ baby?”

“Please don’t stop,” he said, more question than statement.

“Oh, I hadn’t planned on it,” he snickered, “not unless you told me to.”

“Trust me, I want you to keep going,” he begged, too aroused to be embarrassed. 

“Good.  You want me, Wes, really want me?”  Travis’ hips were rubbing against his ass in time to the strokes he was levying on his cock.   

“Yes,” he admitted, “more than you can imagine.”

“You ever been with a man before,” Travis asked, curious.

“Yes,” he groaned, arching his hips forward into Travis’ questing hand, “a few times.”

“Thank God,” Travis muttered.    He lifted Wes’ skirt, bringing his throbbing cock against his partner’s mostly bare ass.  “Shit Wes, a thong too?” 

“So glad you approve,” he teased, wiggling his backside against Travis’ erection, his confidence returning in a rush.  A nervous laugh escaped him suddenly.  “Sorry, was just thinking…”

“About what?”  Travis slid one hand along the muscled curve of a buttock, teasing Wes’ crack with the tip of his fingers.

“That I almost went without tonight.  Figured I wasn’t going out, so why bother.”

He could hear Travis swallow behind him.  “Fuck, you’re going to kill me tonight.”

Wes looked over his shoulder at his partner.  Desire warred with control on his face and he loved how it looked on him.  Travis wasn’t ever one to resist an urge and here he was, doing just that.  He thought about maybe, possibly letting him off the hook.  “Horny enough back there?”

“Drop that pretty little piece of lace and let me show you,” he growled.

With a flirty little smile, Wes did just that.  Turning, he faced Travis, never taking his eyes from his partner’s face while he ran his fingers up his thighs, under his skirt, and worked the red lace thong down over his hips.  He let it fall, pooling at his feet in a delicate little pile of almost underwear.  “Like that?”

“Yeah.  Just like that.”  Travis lifted Wes’ skirt again, fisting his cock.  “You amaze me.  Just when I think I know everything about you, you surprise me.”

Wes gave him a sweet little smile.  “You don’t even know the half of me yet,” he promised.  His teeth buried themselves in his bottom lip when Travis’ grip on his cock tightened, stroking more firmly.  “I can promise you though, you keep doing that and what happens won’t be a surprise.”

Travis gave a throaty chuckle, loosening his grip but not letting go.  Wes leaned in closer, lips brushing tentatively against Travis’, testing to make sure he wasn’t screwing with him.  His partner’s mouth opened, devouring Wes’ lips with his own.  He slid his tongue into Travis’ mouth, exploring and tasting. He let his fingers fall to Travis’ belt buckle.  Working as quickly as his shaking hands would let him, he pulled his belt through the buckle, letting it fall open.

“You’re playing with fire,” Travis mumbled between kisses, “you sure you want this.”

Wes thrust his hips forward, fucking Travis’ hand for a couple strokes.  “What do you think.”

“I think you’re not going to be able to walk in the morning,” he threatened, “but I had to make sure.”

Wes smiled against Travis’ mouth, fumbling for a minute with the button on his jeans before getting them open.  “I’m sure,” he promised, pulling Travis’ jeans all the way open and shoving his hand down inside. 

Travis groaned at the touch of Wes’ smooth fingers on his cock.  “Your hands are so soft,” he panted, desperate for as much contact as he could get. 

“The power of a good moisturizer,” he laughed, stroking and teasing his partner. 

“Speaking of which, you had better have some lube around here close.”

“Oh yeah,” he laughed, gripping Travis tighter, getting a similar response from him.  “And why’s that?”

“Because you’re about four seconds from being bent the hell over the back of that couch.”  He rocked his hips forward, pushing his throbbing erection into Wes’ hand for emphasis. 

“Music to my ears,” he teased, releasing Travis and pulling out of his soon-to-be lover’s grip.  “Be right back.”

Travis stood in the living room, cock standing at attention, watching as Wes disappeared into his room, skirt swirling behind him.  “Damn, those heels make his ass look great,” he muttered, not even slightly embarrassed for ogling his partner in such a fashion.  Scrubbing his hands roughly over his face, he tried to reign in his self-control before he spilled like a schoolboy.    

Wes flounced back into the room, tube of go-juice in his hand.  He waved it in front of Travis, smiling.  “This work?”

“You’re about to find out,” he threatened playfully, grabbing the tube from him. 

Travis turned Wes around so that he was facing the couch.  He placed the blonde’s hands firmly on the back, shoulder width apart.  Flipping Wes’ skirt up and onto his back, he stared at his half-naked partner’s smooth, pale skin.  He squeezed some of the thick gel onto the tips of his fingers.  Working them against Wes’ hole, he slid one in slowly.  Wes moved back against Travis’ hand, whimpering.  “Oh, you like that, huh?  You want more?” 

“Please,” he begged. 

“Whatever my pretty little girl wants, she gets.”  He pulled his finger back, returning with two, slowly at first, then faster.  Wes moaned, working his ass back against Travis’ hand, meeting him halfway each time.  “Oh yeah, my baby’s ready, isn’t she?”

“Yes, she is,” Wes agreed, desperation lacing his voice.  “And she needs her man.”

Travis pushed his jeans down until they settled at his knees.  Squeezing more cool lube into the palm of his hand, he coated his cock with it, biting on the inside of his cheek to keep from losing it right then.  He placed the head of his cock at Wes’ entrance, asking again, “Are you sure?”

“Never been surer of anything,” he assured him.

Without another word, Travis slid his cock into his partner’s ass, slowly, before pulling back and thrusting forward again.  “Damn, you’re so fucking tight,” he said.

“It’s been awhile,” he confessed, “but you feel so good, Trav, please…”

“Please what,” he said again, smiling, liking this game. 

“Please fuck me,” Wes said, looking over his shoulder, seeing that look of restraint on Travis’ face again.  “Fuck me hard.”

Travis’ fingers whispered up the backs of Wes’ thighs, coming to rest on his hip bones.  He gripped them tightly, rocking against the blonde a couple times.  “You had better hold on, baby,” he warned before thrusting against him, “’cause I’m not sure how long I can hold on.”

“Give me all you’ve got,” he grunted.  “I’m a big girl, I can take it.”

“And you’re such a pretty girl, too,” Travis cooed.  “So gorgeous in your dress, so much better with it up over your hips like this.  Nothing but that perfect ass of yours and those long, long legs in your sexy little heels.”

Wes’ heart thudded in his chest.  “You like me like this, do you?  Bent over with my ass in the air, waiting for your cock?”  He gave a little wiggle of his hips and was rewarded with a sharp series of thrusts from behind. 

“Oh yeah, baby.  I love it when you are so horny you don’t even wait to get naked to fuck.  Turns me on, _you_ turn me on.”

“And it makes me hot knowing you can’t even get your pants off before you have to be inside me,” Wes admitted, knowing that was the ultimate compliment for him – that Travis hadn’t even bothered to shuck his jeans fully before plowing into him. 

“You are seriously going to kill me,” Travis lamented, pounding his cock hard into Wes. 

“But you’ll die with a smile,” he promised.

“I’m going to hold you to that, blondie.”  

Wes arched back, meeting each thrust of Travis’ hips eagerly.  He wrapped one hand around his cock, jerking roughly as he was taken from behind.  Travis’ movements quickened, became more aggressive, making it harder for Wes to hold himself up with one hand, but he kept at it, determined to come with Travis.

“Fuck yeah, baby,” Travis rumbled in his ear, “jerk yourself off for me, I like that.  So pretty, so freaking hot.” 

Wes obeyed happily.  “Travis,” he mewled, “I’m so close, please…”

“Anything for my gorgeous little girl,” he said, increasing his already frantic pace. 

Travis’ hips slapped roughly against Wes’ ass, drawing grunts of pleasure out of both men.  With an excited shout, Wes came hard, almost losing his grip on the back of the couch.  “I got you, baby,” Travis promised, wrapping an arm tightly around his waist, holding him upright, thrusting rapidly.  He groaned loudly, slamming hard into Wes, before exploding inside his lover. 

Loose-limbed, he fell onto his partner’s back.  Wes’ wrists buckled under the weight momentarily, before he was able to shift and shore himself up on his forearms.  “Travis,” Wes pleaded, “I’m not sure I can hold us both up for much longer.”

He could feel the rumble of laughter move through Travis’ chest before he shifted off of him.  Wes straightened partially before he was whisked around and backed up against the couch.  Travis stood inches from him, face glistening with sweat, eyes filled with something he’d never seen before. 

He straightened Wes’ dress, smoothing the fabric so it laid flat.  “You dirtied your dress, baby.”

Wes snorted.  “I think that was your fault.”

He cupped Wes’ face in his hands.  “I think you’re right.  Maybe that means I need to buy you a new one?  Something blue like your eyes?  Or would you prefer the proverbial little black dress.”

Wes turned away, suddenly embarrassed by this conversation.  “I’m not sure you could afford my tastes, Marks.”

Travis snickered, a dirty, seductive sound that traveled straight to Wes’ cock.  “Oh, I think I can manage your tastes just fine, sweetheart. It’s your clothes I can’t afford.”

Despite himself, he laughed.  “You’ve got that right.”  Wes was quiet for a moment, gathering his thoughts.  “Travis?”

“Yeah,” he muttered, placing kisses along Wes’ jawline.

“Can we keep this between us?”  He lifted a hand, running his fingers through the other’s short, dark hair.  It was a bit longer than usual, he noticed, thinking that he liked it like this.

“Which part?  The sex or the fondness for women’s clothing?”  He bit at Wes’ throat, giving a quick lick to his Adam’s apple. 

“Both,” Wes pleaded weakly, feeling his body wanting to respond to Travis’ touch again. 

“Mmm, I don’t know if I can keep both to myself,” he teased. 

“You’d better or you’ll never see me like this again,” Wes threatened.

 

_So Very Pretty_

“Aw, but baby, I have so many ideas… little black dress… French maid… cheerleader…” His voice trailed off as he busied himself sucking a mark onto Wes’ shoulder.

“I am not your dress up doll,” he argued, less angry than he was aroused by the idea of Travis wanting him in so many outfits, so many ways. 

“Nope, you’re sure not,” he agreed.   “You’re my strip you naked, fuck you silly doll.”

Wes’ knees shook with anticipation.  “I think I can live with that.”

Travis laughed heartily, wrapping both arms around Wes’ middle, pulling him close.  “You ready for more because I think I am.”

“Oh, I know you are,” he joked, rubbing his semi-hard cock against Travis’ groin.  “You know where the bedroom is, right?”

He grinned.  “I sure do.”  With a half bow, Travis scooped Wes into his arms, heels and all, and carried him off. 

“I feel stunning and entrancing,” Wes sang happily, “feel like running and dancing for joy.”

“For I’m loved by a pretty wonderful boy,” Travis finished with a grin.

“You are such a jerk,” Wes scolded.  “You stole my line.”

“Just wait, I’m about to steal your breath away, too.”  He turned into Wes’ bedroom, tossing the blonde onto the bed. 

“I accept that challenge, Travis Marks.”  He lifted one foot in the air and flipped off his shoe.  He raised the other and flipped that one to the floor as well.  “Now, come here and show me what a real man can do for a girl.”

He didn’t have to ask twice.

**Author's Note:**

> Oh good Lord, you made it? Congratulations! You deserve an award, or at least a cookie. ;) Thank you.


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